Potassium Carbonate → t-Butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate

HRID 431729ノート

反応式

HRID 431729 の反応式
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N+:18]([O-:20])=[O:19])=[CH:10][C:9]=1[N+:21]([O-:23])=[O:22].[C:24]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1COCC1>[N+:21]([C:9]1[CH:10]=[C:11]([N+:18]([O-:20])=[O:19])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:24]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])([O-:23])=[O:22]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 169871-Chloro-2,4-dinitronaphthaleneHCID 96345tert-Butyl ethyl malonate

生成物 1

HCID 11452450t-Butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate収率 78.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

K2CO3 (4.04 g, 29.22 mmol) was added to a solution of 1-chloro-2,4-dinitronaphthalene (6.04 g, 23.91 mmol) and t-butyl ethyl malonate (5.0 g, 26.50 mmol) in THF (50 mL), and the mixture was heated reflux overnight. The mixture was cooled and filtered, then the filtrate was concentrated under reduced pressure. Flash chromatography (20-50% AcOEt-Petroleum ether gradient elution) afforded t-butyl ethyl (2,4-dinitronaphthalen-1-yl)malonate (7.6 g, 54%) as a pale red solid. M.p. 86-88° C.; 1H NMR (CDCl3, 500 MHz) δ 8.65 (s, 1H), 8.55 (dd, 0.5, 8.5, 1H), 8.36 (dd, 0.5, 9.0, 1H), 7.89 (dt, 1.0, 8.0, 1H), 7.81 (dt, 1.5, 9.0, 1H), 5.64 (s, 1H), 4.26 (q, 7.0, 2H), 1.44 (s, 9H), 1.24 (t, 7.0, 3H); IR (neat) 2980, 1745, 1537, 1368, 1346, 1306, 1253, 1147, 1027, 850, 832, 801, 774, 761 cm−1. FABMS (NBA) m/z 405 (M+H+, 5).

後処理

  1. temperaturethe mixture was heated
  2. temperaturereflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washFlash chromatography (20-50% AcOEt-Petroleum ether gradient elution)

出典と根拠

ORDレコード
ord-c72f337d4fe748be88c9b2631c84dedf
出典データセット
uspto-grants-2003_12
特許番号
US06660742B2

反応ノート

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